


What Are You Wearing?

by JeremyBearimy



Category: Dead To Me (TV)
Genre: Episode: s01e01 Pilot, F/F, Fluff and Smut, Masturbation, Mutual Masturbation, Phone Sex, Strangers to Lovers, original script
Language: English
Status: Completed
Published: 2020-07-07
Updated: 2020-07-07
Packaged: 2021-03-05 06:22:10
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,410
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25129990
Author URL: https://archiveofourown.org/users/JeremyBearimy/pseuds/JeremyBearimy
Summary: I know I'm not the first and won't be the last to do this, but I wrote this based on some of the lines from the original script that didn't make it into the pilot. Judy realizes it's been a long time since Jen got herself off, and decides that she needs help.
Relationships: Judy Hale/Jen Harding
Comments: 5
Kudos: 136





	What Are You Wearing?

“What are you wearing?” Judy asked. Her voice was soft and raspy. It was comforting, Jen thought. But the question caught her off-guard. Surely she hadn’t heard Judy correctly.

“Huh?”

“What are you wearing?” Judy repeated, just a little bit slower, the flirty edge in her voice more prominent.

Jen swallowed, flustered. Her brain flashing back to the earlier; “You come to this group often?” and “...we can not sleep together…” 

Maybe that was just Judy’s sense of humor, she thought. Fake flirting. She could go along with it, but what if Judy thought she was serious? Quick on her feet, she responded as if she hadn’t picked up on it at all. 

“Uh, a pair of my husband’s sweatpants, and a T-shirt he got for running a 5K for… psoriasis,” Jen said, sounding nonchalant.

“Mmm, slower…” Judy purred.

Jen’s face heated up for a moment, a sensation she hadn’t felt in a very long time. She held back the scoff she wanted to let out, this stranger was  _ not _ seriously making her blush. 

“You’re a weird person, Judy,” she said quickly and flatly. All she got in return was a giggle and a “thank you” from Judy.

Jen was expecting an awkward silence between them, but Judy piped up with “Did your husband really like running? Or did he just hate psoriasis?”

Jen knew Judy was trying to make her laugh, and part of her wanted to, but she was still bitter about Judy making her blush. She wouldn’t be giving her the satisfaction.

Judy took the silence as discomfort from Jen and told her that she didn’t need to talk about Ted if she didn’t want to. Hoping she wasn’t already hurting her chances with this woman.

Jen sighed inwardly, realizing her own pettiness was probably making this woman feel bad. And clearly Judy was good-intentioned. 

“Uh, no, no… he… he liked running. Came to it later in life. He was 40.”

“What made him start?”

“He was… gettin’ doughy.”

“Oh yeah. Men get that middle-aged man puff.”

“Yeah. He was getting a full-on beer-belly. He was getting a beer  _ neck _ .”

“Beer  _ neck _ !”

“I got on him a little, ‘cause he was lazy. And I was physically repulsed by him—“

Judy cut her off, not believing her. “You weren’t.”

Jen was somewhat bothered by this. She  _ was  _ repulsed by him. How could Judy know how she felt about him? Judy wanted to think better of her, she guessed, or better of Ted. All she said in response was “okay”, not wanting to argue about this.

“Go on,” Judy encouraged.

Jen went on to say that he was training for a marathon, and that he was in the best shape of his life when he died, and that she was proud. They went back and forth for a while, Jen realizing that Judy was the first person she  _ really  _ talked to about this. She tried not to drag the boys down with her when she was falling apart, and Chris was always trying to remind her how lucky she was for the time she had with him. Judy didn’t do that, she actually listened, and actually cared. Because she understood, Jen thought, Judy had been through the same.

The two of them spoke like best friends; talking about music, sharing pictures, sharing snacks. Jen hadn’t felt this at-ease in over a year, and she had Judy to thank for that.

As requested, Jen texted a picture of Ted to Judy. 

“Did you get it?” She asked, the pain of looking at a photo of him not nearly as heavy as it usually was. She still felt at-ease. Still laid on her bed on her stomach, kicking her legs behind her like a teenager on the phone with their crush for the first time.

“Is that him?” Judy asked.

_ That’s a stupid question _ , Jen thought, feeling the need to tease her. “No, that’s my other husband.”

“Oh, you have another one? Then you’re fine,” Judy joked, not missing a beat. 

“Yeah, but if something happens to  _ him _ ,” Jen went right along, laughing a bit at her own joke. 

Judy laughed with her, feeling a strong sense of relief knowing she’d made Jen laugh, and that Jen was in the state of mind to make jokes at all.

Jen hadn’t laughed in a  _ long _ time, she realized. “It feels weird to be laughing,” she noted, wondering if Judy could relate.

“I think it’s okay,” Judy reassured her.

Jen decided she was right. She’d earned a laugh. 

“Okay.”

“When do you think it’s okay to start masturbating again?” Judy asked, feeling a bit brave now that she had Jen laughing.

Jen didn’t respond, she felt that unfamiliar-familiar heat in her cheeks again. Judy had her backed into a corner. She was  _ really  _ flustered now, her brain too scattered to come up with a clever retort.

Judy felt only a small hint of regret. She knew Jen was probably flustered. Maybe she was a bit of a prude, Judy thought. She didn’t know Jen very well, she might not talk about these things. “Sorry, I don’t have anyone else to ask,” Judy said sincerely. Realizing she was getting herself into the habit of apologizing whenever she left Jen speechless.

Jen was still trying to string a thought together. Trying to come off confident and nonchalant. She couldn’t remember the last time she had a close girl friend to talk to, she never really talked about these things, but no one ever asked. “No, yeah. I don’t know how to answer that.”

There was a beat of silence from Judy’s end. Judy hoped Jen might add something else, letting the silence sit with this subject up in the air. She knew she had Jen really thinking about this now.

Jen’s face was getting even hotter with the silence that hung between them. It might have been 10 seconds that passed, but it felt like hours, so she spoke again. 

“Not  _ now _ ? I guess,” Jen answered. That was the only answer she could really give her, right? Judy could do whatever she wanted while they  _ weren’t  _ on the phone. But not now. 

Judy was about to leave it, but she was stuck on that response. Jen was just teasing her a minute ago, she could tease back.

“Not  _ now _ ?” Judy laughed, “Did you think I was suggesting masturbating  _ right _ now? While I’m on the phone with you?” Judy kept laughing as she spoke; it was more of a performative laugh, but she laughed. “What hotline did you think you dialed?”

Jen tried to laugh, but she was still red in the face. “Hey, I don’t know, Miss fuckin’ ‘What Are You Wearing’.”

Judy laughed, remembering her own joke. “Oh so you think I’m easy?”

“Well if the shoe fits.”

“Woooow,” Judy chuckled, nodding even if Judy couldn’t see her, impressed by her quips. They both let the laughter fizzle out. Jen was ready for them to move to another subject, but Judy was searching for a way to keep going. She spoke up flatly and said: “I can’t remember the last time I got myself off.”

Jen met her with silence yet again, making the assumption that Judy would apologize and change the subject. But Judy held her ground.

“What about you?” Judy asked somewhat hesitantly.

“Huh?” Jen asked, feigning ignorance. She was chewing on her nail now, rubbing her feet together against her comforter.

“When’s the last time you got yourself off?” Judy asked, heart pounding now, almost wanting to throw her phone across the room during that painful wait for a response.

“Do you seriously need to know that?” Jen bit back at her.

Judy cringed a bit, but held her ground yet again. “Come on. I’m just curious. Like I said, I have no one else to ask. And it’s been a while for me. I wanted to know if that’s normal.”

Jen let out a tired exhale. “Well, how long has it been for you?”

“Like, a whole month I think.”

Jen kept fidgeting, now actually thinking about it. When  _ was _ the last time she touched herself? 

“Dude, that’s not even that long,” Jen said flatly.

“Oh, has it been a really long time for you?” Judy raised an eyebrow. Maybe she was getting somewhere.

Jen was silent again.

“Come on, how long has it been? Now I really wanna know.”

Jen sighed, letting out a small chuckle. “Honestly? I can’t remember. Longer than three months.”

“Oh, my god!” 

“Oh, shut up.”

Judy apologized, realizing she was maybe being insensitive. “But, like,  _ why _ ?”

Jen’s face shrunk up. “I don’t know, I don’t have a great relationship with that whole… with my— can we talk about something else?”

Judy sighed, “If you  _ really _ want to. But I think you should talk about it. I think we should address this right now because I think an orgasm would fix everything.”

Jen laughed sarcastically, “Yeah, will it bring my husband back?”

“I mean, maybe, if it’s a good one.”

Jen rolled her eyes. “Oh, are orgasms bringing back the dead now?”

“Maybe if you used a vibrator…” Judy suggested, smirking at her own joke.

Jen laughed, “You think I don’t have a vibrator?”

Judy’s eyebrows shot up excitedly, “ _ Oo _ , good to know.”

“Shut up,” Jen cringed slightly at the latter end of her sex life with Ted. “Well Ted, uh, had a bad back. So.”

Judy nodded as if Jen could see her, looking unconvinced. “Right, right. So why don’t you put it to good use?” Judy asked, now rubbing her thighs together for relief at the very thought.

Jen was blushing yet again. “I’m sure I will at some point, I appreciate your enthusiasm, but I’m not really my ideal partner right now.”

“Oh,” Judy said with a little bit of realization. “I get that. I’m not my own biggest fan right now either.”

“Kind of a bummer, right? Not very sexy.”

Judy frowned at that. Feeling a bit deflated. “Okay so… maybe you need a second party?”

Jen wrinkled her nose at that. “Are you saying I need to get laid? I don’t think I’m ready for that sort of thing.”

“I’m just saying I think you need to get off.”

“Didn’t we just go over this?” Jen asked, now somewhat annoyed.

“I know, I know.” Judy chewed her lip nervously, knowing what she was about to say could end with Jen hanging up in her ear. “But what if… what if I helped you out?”

Jen’s mouth hung open, did Judy mean what she thought she meant? There was no way. She wasn’t about to embarrass herself. “What? If you’re about to tell me you run a male prostitution ring or some shit like—“

“No. I meant… what if I…  _ helped you out _ . From here.”

Jen’s heart was pounding now. Her chest all the way up to the tips of her ears burning. “You’re kidding.”

“I’m not kidding,” Judy said firmly, her face now even redder than Jen’s. She was really squirming now, fighting the urge to put her hand between her thighs at the very thought.

Jen was about to shut her down, but it had been so long… and she hadn’t felt desired in a long, long time. All she could get out was: “Why…?”

Judy was fidgeting even more. “Uh. Because I care about your sexual health?”

Jen rolled onto her side. “This is weird. I should go to bed.”

“Wait no! No,” Judy said desperately. “Come on… Look, I find you… very attractive. When I saw you there with that tight bun in that pencil skirt I just… well I gave you my number, didn’t I?”

Jen’s mouth hung open, loving the way Judy stroked her ego… the way she made her feel sexy…

Judy spoke up again. “I didn’t call you with this intention… I was gonna work up to it… maybe fifth date...”

“Because you’re not easy, right?” Jen teased.

“Right,” Judy chuckled nervously.

There was an uneasy silence that hung between them. Jen hadn’t given any kind of answer yet, but she hadn’t said no either.

“I really meant it,” Judy reiterated.

“I know,” Jen snapped. “I know but… I’ve never done this.”

Judy swallowed, heat building between her thighs. “Well we’re on the phone already, we’re halfway there.”

Jen snorted.

“Let’s just… I want you to relax, okay? This is for you.”

There was a lingering silence before Jen said “Okay.” She was still chewing on her nail, sliding her legs together awkwardly.

Judy swallowed hard, realizing she had done this maybe twice in her life, and never really needed to take over. She was nearly shaking with nerves, afraid of how this would go but far too excited to back out. 

“Um… what would we be doing if I was there right now?” Judy tried, sounding like a teenage boy. 

“Probably drinking.”

Judy blushed, realizing she’d given her almost nothing to work with and beyond embarrassed of herself. “ _ Jen! _ ”

Jen chuckled, “Sorry, sorry. That was not a good start.”

“I know. Shut up. I’m out of practice.”

“We don’t have to if you don’t—“

“No! No, I want to. Believe me. I’m already… I want to.” Judy blushed at her own words, realizing all of the implications she’d just made.

“Oh. So if I hang up right now I’m gonna give you a serious case of blue balls aren’t I?” Jen asked. The fact that Judy was already so bothered made this all so much more appealing. 

Judy squirmed, “Yeah… something like that. Please don’t hang up.”

“Okay.” Jen said, sounding unbothered, trying to hold some sort of power over Judy. “So. You’re already what?”

“I’m already…” Judy sucked her bottom lip, forgetting out to speak. She couldn’t say she was wet, could she? Not to this brand new person. It felt too early for something so explicit. “I’m just… I want to start.”

Jen raised an eyebrow, smirking a bit knowing that she was the one making this woman feel like this. Judy was thinking about  _ her _ and could hardly contain herself. “You want to start, um…” Jen blinked, summoning courage, “...touching yourself?

Judy’s mouth opened to speak, already going dry. She should have been expecting a response like that and yet it still flooded her with arousal. “Yeah, that. I don’t want to get ahead of myself.”

Jen cracked a grin, “Ahead of yourself or ahead of me?”

“Uh. You, I guess,” Judy admitted. Jen was right, the plan was to help her first, but…

Jen’s grin didn’t fade. She liked this, she was realizing. She had no idea something like this would turn her on so much.

“Well. What’s stopping you? Me?”

Judy was red in the face again, heat building in her lower belly. “Uh, no, I mean… I’m still dressed.”

“Okay, what-“ Jen started to say “what are you wearing?” but wasn’t about to set herself up for a joke about that being Judy’s line. “Um, what do you have on?”

Judy looked down at herself. “Um, a robe- a kimono.”

Jen nodded, “Is that it? Nothing underneath it?”

Judy smacked her lips, “Uhhh… I have a shirt on under it. And panties. I guess,” Judy added, feeling bashful now.

“Then why don’t you take the robe off?” Jen suggested. She wasn’t ready to start bossing Judy around, but she was settling into this a bit.

Judy was nearly speechless. Now she was the flustered one. But she was the one who wanted this, and she wouldn’t be backing down. “Okay… I’ll take it off.” 

Jen could hear her set her phone down in a heap followed by the sound of fabrics shifting and sliding as Judy freed herself from the garment.

Judy picked the phone back up off her bed. “Uh… it’s off…”

Jen smirked again, she didn’t realize she’d be liking this so much. She only had one image of Judy in her head, with her pastel colors and pretty skirt and big earrings and adorable bangs, and now she was trying to conjure up an image of that same woman lying in bed in nothing but a T-shirt and panties, desperately trying not to touch herself. And oh, she loved this image.

“You’re a good listener,” Jen observed. 

“Thanks.”

Jen rubbed her thighs together a bit more at the image in her head, wishing it was more vivid than it was.

“Well. Why don’t you take off the shirt too?” Jen suggested. 

Judy’s eyes widened, surprised at how quickly she asked that. “Oh… yes I’ll do that.”

Jen heard the phone thrown down again, the slide of fabric not nearly as loud as she pulled off her shirt.

Judy felt a flutter of excitement as she pulled her shirt off over her head, now clad in nothing but panties, laid out on her bed like this for a woman she met yesterday. The very thought had her nipples standing at attention, even excited by the slide of fabric over them as she slipped off her shirt. She was already eager for Jen’s next instructions, the ache between her legs growing.

“Okay. It’s off. Maybe I am easy…”

Jen laughed, “Yes, yes you are. How’s it feel?”

Judy chewed her lip, squirming. “It feels good.”

“Chilly at all?” Jen teased.

“No… couldn’t tell that to my nipples though.”

Jen’s eyes widened for just a second, realizing Judy’s nipples were standing at attention for her.

The mere  _ thought  _ of Jen had Judy this aroused. Jen was amazed by this.

“Oh. Are you touching them..?” Jen asked somewhat awkwardly, but too excited at the prospect not to ask.

“No, but, do you want me to..?” Judy asked hopefully. Not wanting to do anything unless she was asked.

Jen raised her eyebrows in surprise. Judy was awaiting her instructions, she realized. Judy wouldn’t be doing anything without her permission. 

“Yes, yes I want you to…” Jen held off from adding “if you want…”

Judy hesitated for a moment before bringing a hand to her breast, trapping a nipple between her fingers and lightly squeezing. She let out a soft hum of pleasure, crossing her thighs hard as the heat built. She knew if she put a hand between her legs now she’d come completely unraveled. Her breathing was loud and heavy already, and she made no attempt to quiet it, knowing that that was all Jen could hear on the other end.

Jen was quickly coming to the conclusion that since Judy couldn’t see her, she could do whatever she wanted. The moment she heard that small groan escape Judy’s mouth she couldn’t resist anymore. She slid her hand down over her sweatpants and found herself gyrating her hips to rub against it. She needed any kind of relief at this point, and the feeling was already divine.

“Mm, isn’t this supposed to be for you?” Judy asked breathily, hand still playing at her breasts and teasing her nipples. “I thought I was supposed to be getting you off.”

Jen tried to hold back her grin, biting down on her bottom lip. “You are…” she said in a low, sultry voice, trying so hard to come off confident about this. Now that Judy knew and that information was hanging in the air, Jen allowed herself to slip a hand under her waistband. There was still a layer of fabric in the way, but this was a lot further than she’d gotten in a long time. And it was comfortable, having her hand trapped against herself like this, feeling the heat of her arousal and the moisture that was already seeping through her underwear.

“ _ Oh _ …” Judy breathed. Jen could hear a hard swallow, knowing her mouth was bone dry. “Um,” Judy allowed herself a small smirk, sucking in her bottom lip at the thought, “so you’re touching yourself… thinking about me…”

“Well who else?” Jen retorted, working herself up even more. She was becoming more desperate and wanton with each stroke of her fingers, starting to forget that she barely knew the person on the other end, just wanting to get off. “What are you doing right now?”

“I’m uh… I’m playing with my nipples, like you asked…” Judy said softly, giving herself a light pinch.

Jen felt another wave of arousal at that, her hand now picking up speed. “ _ Mm, fuck.  _ And what do you want to be doing?”

Judy raised her eyebrows at this, not expecting it. She was trying to choose her words carefully, heart pounding with a mix of nerves and excitement. “I guess I wanna be doing what you’re doing.”

Jen felt another wave at that — Judy essentially seeking her permission — and now she couldn’t help but slip her fingers under the waistband of her underwear. She was getting braver now.

“Do you still have your panties on?”

“Yes…” Judy answered, buzzing with anticipation.

“I think you should take them off.”

“I agree, you’re right.” And with that, the phone was set down again, Judy anxious to free herself of the now-wet material. She peeled them down her thighs and kicked them away triumphantly. “Okay, they're off,” she said as she picked her phone back up, maybe a bit too giddily. 

“Oh…” Jen’s hand sped up now, “ _ Oh, God… _ touch yourself,” she said firmly, having summoned all the courage she had.

“Okay, right, yes, ma’am,” Judy said with an excited grin, letting her hand find it’s way between her legs, soaking her fingers immediately. “Oh, yeah…” Judy sighed, “ _ Mmh _ …”

Jen was getting closer now, but needed some encouragement. “How’s it feel?” She asked.

“Oh…” Judy panted, barely able to speak, “So good… I’m so wet…” she tried, the words coming out of her own mouth bringing her closer as she ground herself against her fingers.

“ _ Shit, _ ” Jen groaned, Judy was wet  _ for her _ , thinking about  _ her _ . She felt sexier than she had in many, many years. That comment nearly put her over the edge.

“Oh, Jesus,  _ Judy _ …” 

Judy picked up her speed at that; at Jen saying her name like  _ that. _ She desperately tried to catch up to Jen, letting herself moan freely into the phone as her hands worked feverishly between her legs, her hips pumping to match them. “Fuck,  _ Jen _ ,” she moaned softly. Now she was catching up, and knew that would put them both over the edge. 

“ _ Oh, God, fuck _ ,” Jen groaned at the sound of own name. Judy moaning in her ear was too much to handle as it was, but the sound of her own name… Jen was tumbling over the edge all at once, hips riding her hand desperately as she let herself pant into her phone. “Fuck, Judy, fuck I’m—  _ oh, God _ .”

Judy worked her fingers harder, her whole body nearly vibrating at the sound of Jen moaning her own name into her ear, clearly about to come for the first time in months at the thought of her alone. Remembering that only made it easier for Judy to follow suit. 

“Jen… oh,  _ God _ …” 

Jen let out array of “fuck”s with the occasional “Judy” thrown in the mix, fucking herself wantonly alone in her bedroom, not caring about what she was saying or the noises she was making, and neither was Judy. She let Judy’s desperate incantations of her own name on the other end help her along. Her thighs were convulsing around her fingers now, her hips bucking as the sensation between her legs came to a beautiful crescendo. “Oh,  _ fuck _ , oh…” she called out as she met her peak, riding her fingers to draw this out as long as she could until she couldn’t handle it anymore. 

She breathed heavily, feeling a sense of calm and relief, listening to the sounds of Judy following right along with her.

Jen could hear Judy whimpering and gasping, even dropping the occasional f-bomb into her ear.

“There you go… that’s it…” Jen said encouragingly.

That sent Judy completely over the edge, she was trembling, her whole body convulsing inwardly as she came hard against her fingers. “Fucking…  _ God,”  _ she whimpered into the phone. She let her head fall back completely against her pillow, breathing heavily as she finally pulled her hand away. “Okay… okay…” she panted.

And they were both silent for a moment, listening to each other breathe, not caring to speak yet but each wondering if the other would speak up first. 

Judy brought her fingers to her mouth and sucked the arousal clean off of them, knowing Jen could probably hear her from the small hitch in her breathing.

Jen kept her hand in the front of her pants, not really moving it, just holding it there for comfort as she set the phone down and pulled her blankets up over herself, rolling onto her side, hand between her thighs and phone by her head.

Judy heard her adjust the blankets and decided to do the same, not bothering to put on any clothes, just snuggling up under her blanket.

“So… Do you feel any better?” Judy asked, finally breaking the silence.

Jen found her face heating up yet again, her bravery falling away. “Uh, yup. Definitely feel better. Like I can fall asleep tonight. Um, do you feel better?”

Judy grinned, satisfied with herself. “Oh, definitely. I’m glad we could help each other out.”

“Right.”

Judy squirmed a bit, not knowing what to say now. “I should let you go to sleep, shouldn’t I? It’s like three in the morning.”

“Wait,  _ no _ ,” Jen pleaded. Then, realizing she sounded pathetic and needy, said a calmer “No… I don’t wanna hang up.”

“Okay.”

There was another brief silence before Jen said: “Thank you. For like… getting me out of my comfort zone. I think I needed that.”

Judy grinned, satisfied with herself. “Well thank you for… giving it a shot. Was a very good time for me too.”

“Right.”

“And I’d do it again,” Judy added. 

Jen chewed her lip, blushing again at the thought. “Alright.”

“Alright,” Judy repeated as if they’d just made an agreement.

Jen yawned. 

“You should really go to sleep.”

“You’re right. But… would you mind staying on the phone?”

Judy smiled softly, endeared. “Sure.”

Jen nodded to herself, feeling vulnerable. “Will you wait until I fall asleep? Like, all the way asleep?”

“Of course.”

“Thank you,” Jen muttered, putting the phone on speaker and setting it down. A small grin tugging at her lips as she drifted off easily, peacefully.

**Author's Note:**

> Hope you enjoyed! Decided to make this one separate from my series since it's my first one-shot. Feedback always appreciated.


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